Hmmmmmmmmm Debian (the sensible choice) or Arch (the slightly more interesting one)?
Just as one example, sysvinit - systemd migration took some careful file editing not to botch things remotely. At one point, merging all binaries in /usr/bin incentivized me to move from the no longer supported GRUB-legacy to GRUB2. GRUB2 installer failed leaving a zombie process that prevented anything from touching the mbr...
I wiped it, installed Wheezy and I can tell you that it requires far less maintenance and you can still pull bits and pieces from testing if you really want to.